Anna Maria Vacation Rentals
Our Anna Maria vacation luxury vacation rentals offer the perfect spot for a relaxing beach escape. Our carefully-curated selection of homes include a variety of high end amenities to ensure you have a relaxing stay. Whether you're looking for a pet friendly stay, a waterfront home, or a place with a private pool, you'll find it here at Once Upon a Beach.
Book one of our Anna Maria vacation rentals and make it your home away from home as you head out on the island to enjoy the beautiful beaches, warm waters, and delightful dining options. And be sure to contact us with any questions! We always love to share our insider tips to help you get the most out of your stay.
Not sure if Anna Maria is right for you? Check out our Bradenton Beach vacation rentals as well as our vacation rentals in Holmes Beach!
19 properties available
Welcome to AMI Peppertree Paradise!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Enjoy a sun-soaked getaway at AMI Peppertree Paradise, where comfort, convenience, and island charm come together for the perfect Anna Maria Island vacation rental!1970 s
Welcome to Sea La Vie Beach House!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.A luxurious 2,825 sq. ft. canal-front home featuring a heated pool, spa, and spacious living areas designed for relaxation and comfort.HIGHLIGHTS: Open Concept Living:&nbs
Welcome to Point's Hideaway!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Spacious Island Retreat with Rooftop Views, Private Pool, and Steps to Bean Point Beach!HIGHLIGHTS: Kitchen, Dining, Living Area: Open-concept design with vaulted ceili
Welcome to Three Little Birds!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Luxury Waterfront Living with Gulf Views, Heated Pool, and Island CharmHIGHLIGHTS: Spacious and Open Layout: Living, dining, and kitchen areas designed for seamless gathe
Welcome to Sol Mate!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementBright and Beautifully Updated 3-Bedroom Home with Heated Pool & Spa, Walking Distance to Bean Point Beaches and Pine AvenueHIGHLIGHTS: 1,500 Square Feet: Fresh, modern comfort designed for relaxation. Sle
Welcome to The Cottage on Pine!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and comf
Welcome to Sea La Vie!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover the ultimate in luxury island living at Sea La Vie, a custom-built retreat located on the desirable north end of Anna Maria Island. With 2,933 sq. ft. of elegant living space
Welcome to La Buena Vida!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.La Buena Vida is a luxurious 3-bedroom waterfront home on Anna Maria Island, featuring a heated pool, spa, private dock, and easy access to bayside and Gulf beaches, plus shops and
Welcome to Bateman's!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover the ultimate in coastal luxury at Bateman's, a stunning canal-front retreat perfect for families and friends seeking an unforgettable Anna Maria Island getaway.2543 sq
Welcome to A Shore Thing!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience the ultimate island getaway in this waterfront luxury retreat, perfectly situated just moments from the powdery white sands of Anna Maria Island and the charming boutiqu
Welcome to AcquaLuxe!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience unparalleled luxury at AcquaLuxe, a stunning canal-front retreat on Anna Maria Island featuring a heated pool, private dock, gourmet kitchen, and upscale amenities designed
Welcome to A Wave From It All!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and comfo
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